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Cape Cod and the Islands

$210+ Cheap flights from Illinois to Cape Cod and the Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — ACK
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Cheap flight deals from Illinois to Cape Cod and the Islands

Keep the following information in mind while searching for Illinois to Cape Cod and the Islands flight deals. Data was last updated November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$629
(Priceline)

One-way from

$210
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$253
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
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From Illinois to Cape Cod and the Islands
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One-way flight from Illinois to Cape Cod and the Islands
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Highest demand for flights based on searches. 5% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Illinois to Cape Cod and the Islands

Cheapest flights from Illinois to Cape Cod and the Islands
Explore the most affordable flight options available from Illinois to Cape Cod and the Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2025.

This Expedia deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/251:00 pmORD - HYA
1 stop4h 39mJetBlue
Tue 12/27:58 amHYA - ORD
2 stops14h 54mJetBlue
Deal found 11/17$639
This Expedia deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:25 amORD - MVY
1 stop8h 20mJetBlue
Mon 12/810:10 amMVY - ORD
1 stop10h 33mJetBlue
Deal found 11/19$679
This Mytrip deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/53:26 pmORD - ACK
3 stops21h 43mMultiple Airlines
Tue 12/92:16 pmACK - ORD
3 stops32h 32mMultiple Airlines
Deal found 11/20$743
This Expedia deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:45 amORD - HYA
2 stops9h 35mJetBlue
Sun 12/2112:07 pmHYA - ORD
1 stop7h 39mJetBlue
Deal found 11/18$754
This Kiwi.com deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:36 amORD - HYA
1 stop27h 34mMultiple Airlines
Sun 12/77:58 amHYA - ORD
2 stops15h 26mMultiple Airlines
Deal found 11/17$834
This Priceline deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amORD - MVY
1 stop5h 23mJetBlue
Sun 12/71:34 pmMVY - ORD
1 stop7h 09mJetBlue
Deal found 11/18$845
This Mytrip deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:10 amORD - ACK
3 stops30h 00mMultiple Airlines
Mon 12/83:00 pmACK - ORD
3 stops31h 48mMultiple Airlines
Deal found 11/19$917

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Cape Cod and the Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 20, 2025.
Use the filters below to find and compare flights from Illinois to Cape Cod and the Islands that are best for you.

Fly from

Illinois

Fly to

Cape Cod and the Islands

Route

Depart

Return

Price

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Thu 1/8

7:45 am-3:35 pm

1 stop6h 50m

West Tisbury Martha's Vineyard

Sun 1/11

1:28 pm-5:44 pm

1 stop5h 16m

$629

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 11/25

1:00 pm-6:39 pm

1 stop4h 39m

Hyannis Barnstable

Tue 12/2

7:58 am-9:52 pm

2 stops14h 54m

$639

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Thu 12/4

11:25 am-8:45 pm

1 stop8h 20m

West Tisbury Martha's Vineyard

Mon 12/8

10:10 am-7:43 pm

1 stop10h 33m

$679

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Fri 12/5

3:26 pm-2:09 pm

3 stops21h 43m

Nantucket Memorial

Tue 12/9

2:16 pm-9:48 pm

3 stops32h 32m

$743

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 12/20

6:45 am-5:20 pm

2 stops9h 35m

Hyannis Barnstable

Sun 12/21

12:07 pm-6:46 pm

1 stop7h 39m

$754

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 12/3

8:36 am-1:10 pm

1 stop27h 34m

Hyannis Barnstable

Sun 12/7

7:58 am-10:24 pm

2 stops15h 26m

$834

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Wed 12/3

7:00 am-1:23 pm

1 stop5h 23m

West Tisbury Martha's Vineyard

Sun 12/7

1:34 pm-7:43 pm

1 stop7h 09m

$845

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Thu 12/4

7:10 am-2:10 pm

3 stops30h 00m

Nantucket Memorial

Mon 12/8

3:00 pm-9:48 pm

3 stops31h 48m

$917

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 2/18

10:00 am-5:20 pm

1 stop6h 20m

$223

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 2/17

10:00 am-5:20 pm

1 stop6h 20m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 38 results
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Best time to book a flight from Illinois to Cape Cod and the Islands

Have a flexible travel schedule? Discover the best time to fly to Cape Cod and the Islands from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Cape Cod and the Islands
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Cape Cod and the Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to Cape Cod and the Islands?

    Airlines like JetBlue fly from Illinois to Cape Cod and the Islands in about 6h 50m. The time it takes to get you to your destination can typically vary by up to . The distance between Illinois and Cape Cod and the Islands is about 891 mi.

  • Can I find deals for flights from Illinois to Cape Cod and the Islands that include hotel bookings?

    Yes. In addition to deals on Illinois to Cape Cod and the Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Cape Cod and the Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Cape Cod and the Islands.

  • Can I find deals for business class flights from Illinois to Cape Cod and the Islands?

    Yes. Cheapflights offers flight deals from Illinois to Cape Cod and the Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Illinois to Cape Cod and the Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Illinois to Cape Cod and the Islands

Discover the top 3 airlines that operate flights from Illinois to Cape Cod and the Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$162Average$461FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$304Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$319Average$548FlexibilityNo cancel feeOn-time71%

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